Journal Article Chirality recognition of winding vine-shaped heterobiaryls with molecular asymmetry. Kinetic and dynamic kinetic resolution by Shi's asymmetric epoxidation

Maruhashi, Kazuki  ,  Okayama, Yoichi  ,  Inoue, Ryo  ,  Ashida, Shiomi  ,  Toyomori, Yuka  ,  Okano, Kentaro  ,  Mori, Atsunori

8p.1704 , 2018-01-26 , Nature Publishing Group
The chirality of winding vine-shaped heterobiaryls with molecular asymmetry is recognized by a sugar-based chiral oxidant. Kinetic resolution of (±)-bisbenzoimidazole bearing an olefin moiety takes place with Shi's asymmetric epoxidation to observe k(rel) value up to ca. 35 affording the corresponding epoxide. The reaction of a (±)-bithiophene derivative also recognized the chirality to give the corresponding epoxide with er of 96:4 at 39% conversion. Dynamic kinetic resolution is found to take place when unsymmetrical biaryl composed of benzoimidazole/thiophene is subjected to Shi's epoxidation, whose conversion of the racemic substrate exceeds to 50%.

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